Vinclozolin
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MedKoo CAT#: 461406

CAS#: 50471-44-8

Description: Vinclozolin is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards.


Price and Availability

Size Price Shipping out time Quantity
250mg USD 210 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-04-08. Prices are subject to change without notice.

Vinclozolin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 461406
Name: Vinclozolin
CAS#: 50471-44-8
Chemical Formula: C12H9Cl2NO3
Exact Mass: 284.9959
Molecular Weight: 286.1
Elemental Analysis: C, 50.38; H, 3.17; Cl, 24.78; N, 4.90; O, 16.78


Synonym: Vinclozolin; Ornalin; Ronilan; Vorlan;

IUPAC/Chemical Name: 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione

InChi Key: FSCWZHGZWWDELK-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3

SMILES Code: O=C(N1C2=CC(Cl)=CC(Cl)=C2)OC(C)(C=C)C1=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.03.00


References

1: Salleh N, Giribabu N, Feng AO, Myint K. Bisphenol A, Dichlorodiphenyltrichloroethane (DDT) and Vinclozolin Affect ex-vivo Uterine Contraction in Rats via Uterotonin (Prostaglandin F2α, Acetylcholine and Oxytocin) Related Pathways. Int J Med Sci. 2015 Oct 27;12(11):914-25. doi: 10.7150/ijms.11957. eCollection 2015. PubMed PMID: 26640411; PubMed Central PMCID: PMC4643082.

2: Wu YH, Wu TM, Hong CY, Wang YS, Yen JH. Screening differentially expressed genes in an amphipod (Hyalella azteca) exposed to fungicide vinclozolin by suppression subtractive hybridization. J Environ Sci Health B. 2014;49(11):856-63. doi: 10.1080/03601234.2014.938556. PubMed PMID: 25190560.

3: Aquilino M, Sánchez-Argüello P, Martínez-Guitarte JL. Vinclozolin alters the expression of hormonal and stress genes in the midge Chironomus riparius. Aquat Toxicol. 2016 May;174:179-87. doi: 10.1016/j.aquatox.2016.03.001. Epub 2016 Mar 4. PubMed PMID: 26966872.

4: de Oca FG, López-González Mde L, Escobar-Wilches DC, Chavira-Ramírez R, Sierra-Santoyo A. Vinclozolin modulates hepatic cytochrome P450 isoforms during pregnancy. Reprod Toxicol. 2015 Jun;53:119-26. doi: 10.1016/j.reprotox.2015.04.010. Epub 2015 Apr 28. PubMed PMID: 25929820.

5: Gillette R, Miller-Crews I, Nilsson EE, Skinner MK, Gore AC, Crews D. Sexually dimorphic effects of ancestral exposure to vinclozolin on stress reactivity in rats. Endocrinology. 2014 Oct;155(10):3853-66. doi: 10.1210/en.2014-1253. Epub 2014 Jul 22. PubMed PMID: 25051444; PubMed Central PMCID: PMC4164929.

6: Auxietre TA, Dumontier MF, Balguy I, Frapart Y, Canivenc-Lavier MC, Berges R, Boudalia S, Auger J, Corvol MT, Savouret JF. Sub-NOAEL amounts of vinclozolin and xenoestrogens target rat chondrogenesis in vivo. Biochimie. 2014 Apr;99:169-77. doi: 10.1016/j.biochi.2013.12.001. Epub 2013 Dec 12. PubMed PMID: 24333988.

7: Lor Y, Revak A, Weigand J, Hicks E, Howard DR, King-Heiden TC. Juvenile exposure to vinclozolin shifts sex ratios and impairs reproductive capacity of zebrafish. Reprod Toxicol. 2015 Dec;58:111-8. doi: 10.1016/j.reprotox.2015.09.003. Epub 2015 Sep 28. PubMed PMID: 26423773.

8: van Ravenzwaay B, Kolle SN, Ramirez T, Kamp HG. Vinclozolin: a case study on the identification of endocrine active substances in the past and a future perspective. Toxicol Lett. 2013 Dec 16;223(3):271-9. doi: 10.1016/j.toxlet.2013.03.029. Epub 2013 Apr 1. PubMed PMID: 23558297.

9: Paoloni-Giacobino A. Epigenetic effects of methoxychlor and vinclozolin on male gametes. Vitam Horm. 2014;94:211-27. doi: 10.1016/B978-0-12-800095-3.00008-0. Review. PubMed PMID: 24388192.

10: Schuster A, Skinner MK, Yan W. Ancestral vinclozolin exposure alters the epigenetic transgenerational inheritance of sperm small noncoding RNAs. Environ Epigenet. 2016;2(1). pii: dvw001. Epub 2016 Mar 9. Erratum in: Environ Epigenet. 2016 Apr 14;2(2):dvw004. PubMed PMID: 27390623; PubMed Central PMCID: PMC4933025.

11: Knet M, Wartalski K, Hoja-Lukowicz D, Tabarowski Z, Slomczynska M, Duda M. Analysis of porcine granulosa cell death signaling pathways induced by vinclozolin. Theriogenology. 2015 Oct 1;84(6):927-39. doi: 10.1016/j.theriogenology.2015.05.028. Epub 2015 Jun 6. PubMed PMID: 26141531.

12: Cho S, Kim J, Lee S, Kim TH. Vinclozolin: 3-(3,5-di-chloro-phen-yl)-5-ethenyl-5-methyl-1,3-oxazolidine-2,4-dione. Acta Crystallogr Sect E Struct Rep Online. 2014 Jun 7;70(Pt 7):o754. doi: 10.1107/S1600536814012781. eCollection 2014 Jul 1. PubMed PMID: 25161548; PubMed Central PMCID: PMC4120555.

13: Alvarado-Flores J, Rico-Martínez R, Adabache-Ortíz A, Silva-Briano M. Morphological alterations in the freshwater rotifer Brachionus calyciflorus Pallas 1766 (Rotifera: Monogononta) caused by vinclozolin chronic exposure. Ecotoxicology. 2015 May;24(4):915-25. doi: 10.1007/s10646-015-1434-8. Epub 2015 Mar 1. PubMed PMID: 25725815.

14: Liu H, Liu D, Shen Z, Sun M, Zhou Z, Wang P. Chiral separation and enantioselective degradation of vinclozolin in soils. Chirality. 2014 Mar;26(3):155-9. doi: 10.1002/chir.22284. Epub 2014 Feb 4. PubMed PMID: 24497202.

15: Taguchi YH. Identification of aberrant gene expression associated with aberrant promoter methylation in primordial germ cells between E13 and E16 rat F3 generation vinclozolin lineage. BMC Bioinformatics. 2015;16 Suppl 18:S16. doi: 10.1186/1471-2105-16-S18-S16. Epub 2015 Dec 9. PubMed PMID: 26677731; PubMed Central PMCID: PMC4682393.

16: Knet M, Tabarowski Z, Slomczynska M, Duda M. The effects of the environmental antiandrogen vinclozolin on the induction of granulosa cell apoptosis during follicular atresia in pigs. Theriogenology. 2014 Jun;81(9):1239-47. doi: 10.1016/j.theriogenology.2014.02.005. Epub 2014 Feb 13. PubMed PMID: 24636578.

17: Christen V, Crettaz P, Fent K. Additive and synergistic antiandrogenic activities of mixtures of azol fungicides and vinclozolin. Toxicol Appl Pharmacol. 2014 Sep 15;279(3):455-66. doi: 10.1016/j.taap.2014.06.025. Epub 2014 Jul 11. PubMed PMID: 25019461.

18: Gillette R, Miller-Crews I, Skinner MK, Crews D. Distinct actions of ancestral vinclozolin and juvenile stress on neural gene expression in the male rat. Front Genet. 2015 Mar 2;6:56. doi: 10.3389/fgene.2015.00056. eCollection 2015. PubMed PMID: 25784924; PubMed Central PMCID: PMC4345841.

19: Nakamura A, Takanobu H, Tamura I, Yamamuro M, Iguchi T, Tatarazako N. Verification of responses of Japanese medaka (Oryzias latipes) to anti-androgens, vinclozolin and flutamide, in short-term assays. J Appl Toxicol. 2014 May;34(5):545-53. doi: 10.1002/jat.2934. Epub 2013 Sep 24. PubMed PMID: 24072643.

20: Schneider S, Marxfeld H, Gröters S, Buesen R, van Ravenzwaay B. Vinclozolin--no transgenerational inheritance of anti-androgenic effects after maternal exposure during organogenesis via the intraperitoneal route. Reprod Toxicol. 2013 Jun;37:6-14. doi: 10.1016/j.reprotox.2012.12.003. Epub 2013 Jan 8. PubMed PMID: 23313085.